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The 5-(1,2-dihydroxy-ethyl)-3H-(1,3,4)oxadiazole-2-thione (12) and 1-(5-mercapto-4H- (1,2,4)triazole-3-yl)-ethane-1,2-diol (13) derived from (±) glyceraldehyde (resembles trioses ) have been synthesized from glycerol (1) via a common route. The synthesis of the optical active 5-(2,2-dimethyl-(1,3)dioxolan-4-yl)-3H-(1,3,4) oxadiazole-2-thione (17) and 5-(2,2-dimethyl- (1,3)dioxolan-4-yl)-4H-(1,2,4)triazole-3-thiol (18) may be achieved by the same common route when the D- glyceraldehyde (3) was obtained by cleavage oxidation of 1,2:5,6-Di-O- isopropylidene D-mannitol (15). Similar derivatives 23 and 24 of D-xylose (19) (resembles pentoses) may also be synthesized by the same common route from (tetrahydro-(1,3)dioxino(5,4- d)(1,3)dioxin-4-yl)-methanol (21). This common route provides a simple synthetic pathway to acyclic C-nucleosides and to less extent to cyclic C-nucleosides.

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A common route to the synthesis of 1,3,4-oxadiazole -2-thione and 1,2,4-triazole -3-thiols derivatives of trioses and pentoses as models for acyclic C-nucleosides